Dimethyl (R)-(+)-methylsuccinate

Base Information

• Chemical Name: Dimethyl (R)-(+)-methylsuccinate
• CAS No.: 22644-27-5
• Molecular Formula: C7H12O4
• Molecular Weight: 160.17
• Hs Code.: 2917190090
• DSSTox Substance ID: DTXSID80431434
• Nikkaji Number: J84.160I
• Wikidata: Q72470902
• Mol file: 22644-27-5.mol

Synonyms:22644-27-5;Dimethyl (R)-(+)-methylsuccinate;(R)-dimethyl 2-methylsuccinate;dimethyl (2R)-2-methylbutanedioate;(R)-PYROTARTARIC ACID DIMETHYL ESTER;(R)-(+)-Methylsuccinic Acid Dimethyl Ester;(r)-dimethyl methylsuccinate;Dimethyl (r)-methylsuccinate;(R)-dimethyl2-methylsuccinate;SCHEMBL774101;dimethyl (R)-2-methylsuccinate;NFOQJNGQQXICBY-RXMQYKEDSA-;DTXSID80431434;NFOQJNGQQXICBY-RXMQYKEDSA-N;(R)-2-Methylsuccinic acid dimethyl;AKOS015840301;AS-38247;Dimethyl (R)-(+)-methylsuccinate, 99%;CS-0204538;(R)-(+)-METHYLSUCCINICACIDDIMETHYLESTER;1,4-DIMETHYL (2R)-2-METHYLBUTANEDIOATE;d-I+/--MethylbernsteinsA currencyuredimethylester;J-014795;InChI=1/C7H12O4/c1-5(7(9)11-3)4-6(8)10-2/h5H,4H2,1-3H3/t5-/m1/s1

Chemical Property of Dimethyl (R)-(+)-methylsuccinate

Chemical Property:

• Vapor Pressure: 0.408mmHg at 25°C
• Melting Point: 140-145 °C (decomp)
• Refractive Index: n20/D 1.419
• Boiling Point: 195.999 °C at 760 mmHg
• Flash Point: 83.333 °C
• PSA: 52.60000
• Density: 1.076 g/cm³
• LogP: 0.35860
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 160.07355886
• Heavy Atom Count: 11
• Complexity: 153

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dimethyl (R)-(+)-methylsuccinate 99% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(=O)OC)C(=O)OC
• Isomeric SMILES: C[C@H](CC(=O)OC)C(=O)OC
• Uses: Dimethyl (R)-(+)-methylsuccinate can be used in the synthesis of FK-506, a macrolide generally produced by Streptomyces tsukubaensis.

Technology Process of Dimethyl (R)-(+)-methylsuccinate

There total 120 articles about Dimethyl (R)-(+)-methylsuccinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

methyl (3S)-4,4,4-trimethoxy-3-methylbutanoate (1283688-51-6) → (S)-dimethyl 2-methylsuccinate (1604-11-1,21307-96-0,22644-27-5,63163-08-6)

Guidance literature:

With hydrogenchloride; water; In diethyl ether; for 0.166667h;

DOI:10.1016/j.tetasy.2010.12.014

Reference yield: 99.0%

mesaconic acid dimethyl ester (617-53-8) → (S)-dimethyl 2-methylsuccinate (1604-11-1,21307-96-0,22644-27-5,63163-08-6)

Guidance literature:

With formic acid; TETRACYCLINE; paraquat dichloride; In water; at 40 ℃; for 100h; Clostridium formicoaceticum;

DOI:10.1016/S0040-4020(01)85677-5

Reference yield: 23.0%

Dimethyl itakonate (617-52-7) → 3-methyltetrahydrofuran (13423-15-9) + dihydro-4-methyl-2(3H)-furanone (64190-48-3,65284-00-6,70470-05-2,1679-49-8) + methyl 2-methylsuccinate (21307-96-0,22644-27-5,63163-08-6,1604-11-1) + 3-methyltetrahydro-2-furanone (1679-47-6)

Guidance literature:

With C₄₅H₄₅P₃Ru; hydrogen; bis(trifluoromethanesulfonyl)amide; at 200 ℃; for 0.0833333h; under 75007.5 Torr; Autoclave;

upstream raw materials:

diazomethane

2-(R)-methylsuccinic acid

methyl <1-((E)-styryl)ethyl>acetate

methyl 2-methylsuccinate

Downstream raw materials:

2-methyl-1,4-butandiol

2-Methyl-bernsteinsaeure-dihydrazid

(R)-2-methylsuccinate-1-monomethyl ester

L-malic acid methyl ester

Refernces

• 1、 Vallianatou, Kalliopi A.,Kostas, Ioannis D.,Holz, Jens,B?rner, Armin. "Me-AnilaPhos: a new chiral phosphine-phosphoramidite ligand for a highly efficient Rh-catalyzed asymmetric olefin hydrogenation". . p. 7947 - 7950. Retrieved 2006.
• 2、 Lyubimov,Petrovskii,Davankov. "New ionic phosphite ligands: Synthesis and application in asymmetric Rh-catalyzed hydrogenation". . p. 528 - 531. Retrieved 2009.
• 3、 Gavrilov, Konstantin N.,Shiryaev, Alexei A.,Chuchelkin, Ilya V.,Zheglov, Sergey V.,Rastorguev, Eugenie A.,Davankov, Vadim A.,Boerner, Armin. "BINOL-derived diphosphoramidites bearing unsymmetrical 1,2-diamine link and their application in asymmetric catalysis". . p. 1052 - 1057. Retrieved 2012.
• 4、 Doyle, Abigail G.,Gandhi, Shivaani S.,Jiang, Shutian,Kariofillis, Stavros K.,Martinez Alvarado, Jesus I.,?urański, Andrzej M.. "Using Data Science To Guide Aryl Bromide Substrate Scope Analysis in a Ni/Photoredox-Catalyzed Cross-Coupling with Acetals as Alcohol-Derived Radical Sources". supporting information. p. 1045 - 1055. Retrieved 2022/01/19.
• 5、 -. "Chiral ferrocene phosphine-indole aminophosphine ligand as well as preparation method and application thereof". Paragraph 0052-0053. . Retrieved 2021/05/22.